We’ve written a lot of articles on this blog about travel jobs, how to get paid to travel, where to find remote work and how to make money online, but how exactly did we manage to create a business while travelling the world?
How did we go from working 12 hour shifts at our jobs in Canada, with only 2 weeks holiday per year, to travelling full-time, working 15 hours per week and earning more than we ever did at home?!
This is a question that we get asked a lot and while we can share with you many different jobs that you can do remotely, I know that a lot of you really want to know how we did it.
How we saved up money for our first ever world trip. How we figured out how to make money on the road. What we did when we ran out of money. And, how we sustained our travels at first, when we were hardly making anything at all.
We’ve now spent over a decade on the road and we’ve created a lifestyle for ourselves that neither of us could have dreamed of. We had no prior experience in online business, teaching english or even in travel, but we made it work.
In this article I’m going to share with you our journey to location independence and how it completely changed our lives and the way we see the world.
The Decision To Make a Change
It wasn’t like we had a terrible life in Canada. Looking back now, after having met people in countries we visited with far less, I now know that we had it very well. Dariece and I both had well-paying jobs, we owned a house, a car and had quite a few “things”. We had a circle of friends, supportive family members and we had each other.
The problem was, we simply weren’t cut out for the monotony of home life. I worked long hours in order to make the money I made, and Dariece had a lot of stress, dealing with multi-million dollar contracts and mortgage closings at her job as a paralegal.
We both wanted to travel, but our measly 2 week vacation time per year simply wasn’t enough to do anything besides a quick holiday down to Mexico (which we managed once).
I didn’t like my job. I loved the people I worked with and I enjoyed the pay checks, but I felt depressed every single Sunday night when I knew I had five 12 hour shifts to conquer before I saw another day off. The work was strenuous and unfulfilling, but it paid well. So, like so many other Canadians, I stuck with it because of the financial security it offered.
Dariece liked her job more than I did, but she still hated going into work on Mondays and we both came home stressed and exhausted every night. I was working a lot of graveyard shifts so we didn’t see each other very often, and when we did, we’d usually be so tired that we’d just sit on the couch and watch TV.
We knew we wanted a change, but back then there weren’t a lot of people just quitting their jobs and hitting the road. “Gap Years” aren’t a popular thing in Canada (like they are in the UK and Australia), so we’d never really even considered saving money and leaving for an extended period of time.
One day, after a particularly stressful shift at work, I came home exhausted, but instead of sitting on the couch like I normally did, on this day I went on the computer. I just wanted to escape. I was so sick and tired of working for someone else and I felt like there had to be more to life than work, eat, sleep, party on weekends and repeat.
I started researching travel (as one does when they’re tired of work). I think we’ve all sat at work and stared at that same screen saver of that same beach in the Maldives and wished we could teleport to the sun loungers and order a cocktail delivered to the sand.
But on this (fateful) day, instead of searching for cheap holidays, I started researching how to travel for a longer time. I’d heard of people “backpacking” but I had no idea what it meant. How much does it cost? How do you save money for a trip like this? Where are the cheapest countries to visit? Can you do it with no prior travel experience.
This took me down a rabbit hole of pioneer travel bloggers like Nomadic Matt and Expert Vagabond who had somehow figured out how to travel for a year or more at a time.
At that time, there were very few travel bloggers and of them, not many were making a real living, so a lot of the posts I was reading were just about how to travel on very little money and how to get from place to place.
I still had no idea that we could actually make a living while on the road, so in my head I had decided that I wanted to save up my money and go travelling for a year. By the time Dariece came home from work I was fully engulfed in my research. She walked into the room and without even saying hello, I simply said:
“If you could travel to anywhere in the world for an entire year, where would it be?”
Without missing a beat her response came swiftly and confidently:
We didn’t know it at the time, but those two sentences, spoken without much thought at all, had completely changed our lives. Dariece sat down next to me at the computer and we both continued down the rabbit hole of long-term travel together.
Within 8 months we had saved up enough money, sold our house, sold our car, stored the remainder of our belongings and left for Southeast Asia.
How We Prepared
Preparing for this trip didn’t come easy. There were always doubts in our heads like:
Are we crazy?
What if we never get good jobs like these again?
How are we going to sell all of our things?
What if we run out of money completely?
These were all completely rational thoughts, but we knew that if we didn’t make this happen now, we may lose the opportunity to travel forever. We wanted to see the world, and we were determined to make this trip happen.
The first thing we did is set up an automatic withdrawal from both of our accounts into a travel savings account. This account was not a special type of account, it was just a separate joint savings account that we could both put money into. (At the time, we weren’t sharing money. We hadn’t been together for very long!)
We wrote out all of our expenses (including mortgage, car insurance, electricity, food, gas etc.), and then subtracted that number from our earnings. We then gave ourselves $50 / month for entertainment. Whatever money was left over after paying for our essentials, we would put into that travel savings account — every penny of it.
While we were calculating our expenses, we noticed that not all of them were 100% necessary, so we cut back our cable TV to the cheapest possible plan, as well as our cell phones, internet, insurance and pretty much everything else we could cut. We were like Wal-Mart rolling back prices, but we were rolling back the expenses of our lifestyle in Canada, so that we could live a better life on the road later on.
I also took as many overtime shifts as I could. Any extra money we had above and beyond our $50 entertainment budget, we’d put directly into the travel savings account.
Click Here to read more about how we were able to save $40,000 CAD in one year living in Canada.
Selling The House
This was a really stressful part of this whole process. Dariece had purchased a house with a friend as an investment and had fallen in love with it. We both lived in it together and it was a beautiful place, right downtown in Calgary. But after calculating the cost of a property manager, the mortgage, and what we could make if we rented it out, we realized we’d be losing money each month (this is before Airbnb).
Dariece knew we had no choice but to sell it, but every week the housing market was dropping.
That day when we decided to travel to Southeast Asia for a year was in February of 2008. The global financial crisis was already looming on the horizon, and this was yet another doubt we had in our heads and another excuse not to go. But we pressed on.
Luckily, thanks to its excellent location, we were able to sell the house at around $18,000 profit. I also sold my car for $8,000, so together by the time we left we had around $40,000 CAD including our savings.
Storing our Stuff
This was another massive stress, but just as many things did during this transition period, a new path opened up that allowed us to get past this hurdle.
We had looked into storage facilities and they were expensive. We knew that with our savings, we were already going to barely be able to go for a year, especially considering the fact that we both wanted to come back with at least $7,000 in the bank in case we couldn’t find work.
Just as we were about to pay an exorbitant amount of money to store things that we would ultimately never see again, my brother purchased a business which happened to come with a few massive storage containers. Perfect! We stored the rest of the things that we hadn’t sold in this new space and we were one step closer to leaving.
Telling Our Friends and Family
This was another major milestone on our journey towards leaving home for the first time. We waited months before we broke the news to our friends and family. We wanted to make sure that the plan was actually feasible, that we’d be able to save enough money and that it wasn’t just a pipe dream that came from a bad day at work.
Luckily all of our friends and family were extremely supportive. They all urged us to go and were excited for us, though I’m sure in the back of some of their minds, they were doubting that it would work out. The timing couldn’t have seemed worse to them, plus, Dariece and I had only been dating for a little over a year.
Canada and the rest of the world was falling into what news broadcasters were calling the next depression, and people everywhere were losing their jobs.
Still… we pressed on.
I really can’t express the feeling we felt when we were sitting at the Vancouver airport waiting to take off on this incredible adventure. After a very teary goodbye with my mom, we just sat slumped in airport chairs in shock.
Were we really doing this?
By the time the plane wheels left the tarmac, this unimaginable feeling of relief and accomplishment came over us both. I will never forget the feeling and I still get goosebumps thinking about it to this day. It was like a heavy blanket was being lifted off my entire body that I didn’t even know was there in the first place.
There we were, two 24-year-olds (I turned 24 that day when we landed in Bangkok) about to embark on the trip of a lifetime and we had no idea what was in store for us. We’d left the norm behind, and to us, we felt like pioneers. We felt crazy for having thought of this idea and we felt blessed to have actually made the dream into a reality.
At that time our minds could only fathom one year on the road. But in that moment, as we sat in our airplane seats 30,000 feet in the air, that one year felt like it was going to be an eternity
When had we ever had one full year to do whatever we wanted? From the time we were in kindergarten, we only had 2 months of summer holidays, and at this point having been out of school for 6 years, working full-time, even two months would’ve felt like a lifetime away from work.
This was a level of freedom we had never felt, and the sensation of being able to do what we want was so intoxicating that I think we became addicted to it, right there on that plane before our trip had even really begun.
Running Out Of Money
Running out of money after a year of travelling is like coming down off of the most euphoric high and suddenly realizing that you have to go back to the real world. A world where we were just about broke. A world that has been in a financial crisis for over a year. A world that we felt like we no longer belonged in.
The crash of returning home was hard and it nearly devastated Dariece. We were so happy to see our friends and family again and for the first few days, it was fun to tell everyone about our travels, but as the novelty of our return home wore off and the reality sunk in that we’d have to go back to work, we both felt lost.
Luckily however, somehow we had both managed to get our same jobs back.
I had called my work from the road, about a week before returning to Canada and I’d managed to snag the only opening available, ahead of more than 200 other applicants who were waiting in line. Had I called a week later, I don’t know what would’ve happened.
Dariece also got lucky and had formed so many great relationships in the legal community that she managed to get her job back, despite a similar long line of applicants.
Even though we received our jobs back, we knew they weren’t going to be permanent. We were going to save as much cash as possible and hit the road again.
I started work about a week after returning to Canada, but to my surprise I was lit with a new energy. I no longer had the same feeling about money. In the past, money had always meant I could buy new possessions. Money was status. Money was my car, our house, our big screen TV, our security.
But now money was freedom. Money was experiences that I could have on the road. Money held no status, and yet it held the key to my exit from a world that I no longer understood.
While my co-workers were still negative and complained every day, I was happy. I think it drove them nuts!
All I could think was that every hour I spent working, I could put that money towards a scuba dive in Thailand, a motorbike rental in Laos, a waterfall tour in Cambodia. Every overtime shift was a week on the road and every week I spent at work was another week closer to our departure date.
Dariece had a harder time returning to work. At first she was depressed and couldn’t see the light at the end of the tunnel. But slowly, together, we both managed to save up money again.
This time I worked even more overtime shifts. My new-found love for travel kept me at work 70-80 hours per week, pretty much every week for an entire year. Dariece took on freelance work which she could do at home and we both crawled our way back to our goal of leaving Canada on an even longer trip.
We’re Not Coming Back
After 13 months of being home and working long hours, we had managed to save $75,000 CAD. This was more than 60% of our take home wages for the year. We had to accept even more sacrifices, and were on a very tight budget, but we had a few lucky breaks as well (one of our friends left Canada and offered us a place to stay for a very discounted rate).
This time we sold even more of our things and we decided that this money would be enough to last us 2 years on the road, but when it ran out, we weren’t going to go back home. This time we were going to find a way to make it work. We weren’t going to live in Canada again.
We took off on February, 2011 and haven’t resided in Canada since.
That trip took us backpacking around Africa, The Middle East, Northern Asia, the Subcontinent, Southeast Asia and Europe. Again, it was an incredible, eye-opening adventure.
Starting The Blog
After over a year on the road, we still hadn’t made any steps towards figuring out what we were going to do when we ran out of money again. We were basically just travelling and having the time of our lives without really thinking about it.
One day at an internet cafe in India (this was in 2011 when you still had to go to internet cafes to check emails), Dariece stumbled across Johnny Ward’s blog. In one of his “Motivational Monday” blog posts, he talked about how he had grown his traffic and was now making $3,000 per month from his blog.
$3,000 / month???!!
Dariece quickly turned to me and said:
“We have to do this. We are starting a travel blog.”
Of course, neither of us had any idea how to even get started. We’d never edited a website, we didn’t understand code and we could barely even manage to write and send emails. Not to mention we were terrible photographers. We were total newbies.
Still, despite our complete lack of experience, just 2 months later on February 17, 2012 we started our blog Goats On The Road on Koh Phangan Island in Thailand.
After a year and a half on the road, we had run out of money. This time we had run out much sooner than we had anticipated and the thought of going back to Canada a full 6 months sooner than we had planned nearly broke Dariece.
By now we were supposed to be in China, working as English teachers, but with the bank accounts stretched to the final few weeks of travel, we were sitting on a beach in Thailand not knowing what to do next. We had only just started our blog and at this point it was a distant dream to one day actually make a few dollars from it.
Dariece broke down in tears as the thought of ending this lifestyle that we were so in love with sunk in. I didn’t know what to say to her but I knew she needed a solution so I said:
“Listen, we’ll book flights to China now. We’ll hand out resumes to every school in the country until we find a job. We’ll make this work.”
This seemed to comfort her for the time being and even though I had no idea how we were going to make it work, we booked our flights and headed to China a few days later.
This was our first step towards a location independent life, and we loved it. Upon landing in China we had started (virtually) handing out resumes and calling every “Teacher Wanted” ad that we saw posted at hostels, cafes and restaurants. After just a week we had landed a job at a school in Yangzhou, China. We were ecstatic.
Not only did this mean that we wouldn’t run out of money, it meant that no matter what happened, we’d always have teaching English to fall back on. So long as we didn’t want to return to normal life in Canada, we could teach English around the world.
This was a massive weight lifted and finally Dariece’s breakdown was in our rear view mirror and we had taken our first steps towards a somewhat location independent lifestyle. We spent a year teaching English in China, and it was a wonderful experience.
The Blog Starts Making Money
In June of 2013 we made our first “real money” from the blog. One of my favourite bloggers at the time, Nomadic Samuel, added us to a Facebook group where other bloggers (far more established than us), shared advertising contacts. While we didn’t contribute nearly as much as we benefited, after having our blog for just over a year, we made $585 in the month.
By the time our teaching contract was up in July of 2013, the blog was earning between $600 – $1,100 CAD from advertising, mostly in the form of sponsored content.
We Hear About House Sitting
Most journeys towards location independence come with stepping-stones. Very few of us simply quit our jobs and start making enough money to support our travels right away. Most of the people who are now location independent had these kinds of stepping-stones along the way that allowed them to save a bit of money, or make a bit of side money, while the ultimate dream of an online business slowly nears.
For us, house sitting was a major stepping stone and it came at the perfect time. We found our first house sitting job on the Caribbean island of Grenada through TrustedHouseSittters.com. We were amazed that after just a few weeks of having our profile online, the owner of this beautiful home and lovely dog had contacted us and asked us to stay.
By the time we started the house sitting job in April of 2014, the blog was making around $1,500 / month on average, with some months as high as $2,500 and some as low as $500. Needless to say, the blog income was very unstable at this time, so the free housing and vehicle (in exchange for taking care of our new furry friend) was the perfect buffer for our lack of finances.
Another stepping stone that we found while we were house sitting in Grenada, was that we could write articles for other websites and get paid. We spent months pitching different blogs and sites and eventually found a few that were willing to pay us to write a set number of articles each month. This gave our blog a bit of stable income and I believe with all of our freelance together, we had a base income of around $1,000… which helped a lot.
We Work On Our Blog While House Sitting
House sitting not only gave us the savings we needed to survive on our fledgling blog’s income, but it also gave us the time to stop travelling every day and to sit down and focus on the website. We spent 6 months in Grenada during that first house sitting job and in that time we managed to grow the blog to a level where we felt like it could actually sustain us long-term.
Hitting Income Milestones
As the blog grew over the years, we started hitting financial milestones. The first and most important was making it to $3,000 USD. That’s the amount that Johnny Ward had written about earning way back in August of 2011. When we had read that post in December of 2011 in that internet cafe in India, it set a goal in our minds.
As our blog started to grow, so too did our horizons. We started to think that this thing could actually be a business one day, but still we took it one step at a time.
We didn’t consistently hit $3,000 per month until around the middle of 2015. By this time we had been blogging for over 3 years and had been spending on average 20 hours per week on the website. When we reached this point in our blogging journey, we rejoiced. At this point the blog was making decent income from affiliates, our freelance work and some direct advertising.
The income only continued to grow over the years and we’re happy to say that, our website is now one of the most trafficked travel blogs online, and the income we’re earning now is far more than our salaries in Canada.
Back when we started, travel bloggers would’ve dreamed of making six-figures a year, but these days there is so much more opportunity for brand partnerships, advertising and press trips. That’s why I always tell people that the market isn’t too saturated to start your own travel blog today.
Sure, there’s a lot more bloggers and you have to carve out a more narrow niche than just “travel blogger”, but there is much more money being spent in the online space than there was when we started. Now is the best time to launch your website.
I still can’t believe how far we’ve come over the past 10 years. From quitting our jobs in Canada and travelling on a super-tight budget through Southeast Asia, to creating our own online business that hires nearly a dozen people around the world. It feels very surreal.
I often think, what if I could go back to before we left on the first trip and talk to myself. What if I could time travel to those moments when Dariece and I were stressed about selling the house in a diving market, or when we were exhausted from working overtime shifts and I told myself that this current lifestyle was on the horizon.
Or what if I could travel back to that breakdown that Dariece had on the beach in Thailand and instead of giving her the generic band-aid of teaching English, I explained that in just a few years we’d be making more money and living a better life than we ever thought possible.
In my opinion, being location independent is the best thing in the world. Now we wake up when we want, work when (and where) we want, and travel wherever we want. This is all thanks to the internet, to the abundance of information and training online, and to the world of English teaching, house sitting and blogging. And of course, a big thank you to you, our readers for supporting our journey.
I’m so happy that we decided to just go for it.
Now that I look back on that fateful day when I asked Dariece where she’d go for a year, I’m so happy she didn’t hesitate. I’m happy that she had the same mindset as me and was willing to take this journey with me. I’m happy that we had family and friends who supported us and I’m happy with every single thing that happened to us along the way.
I wouldn’t change a thing.
Even the times we ran out of money. Even when we had to go back to work. Even the hours I spent slogging it out at a job I hated. Every single moment brought me here, to this location independent lifestyle and every moment was worth it.
If you’re reading this (extremely long) post and thinking about making a change, but don’t know where to start. Start now. Start here. Don’t put it off any longer. I’m not a motivational speaker. I’m no Tony Robbins. I’m just a guy who has done it, and I know that the only regret I have is not doing it sooner.
Once you start taking steps towards a location-free life, things will start falling into place. Once you take the first steps away from a life of stress and monotony towards a life of freedom, travel and adventure, you’ll feel a shift in the world around you.
Once the plane wheels finally leave the tarmac and you’re off to begin your life on the road, I’m confident that you’ll feel the same blanket lift from your soul.
If you want it, go for it. There’s never been a better time to turn travel into a lifestyle.
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